


How’s this Mr. DeMille?

by Dolavine



Category: Supernatural
Genre: Dean Winchester Cross Dressing, M/M, cross dressing
Language: English
Status: Completed
Published: 2012-12-30
Updated: 2012-12-30
Packaged: 2017-11-23 01:26:09
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,365
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/616543
Author URL: https://archiveofourown.org/users/Dolavine/pseuds/Dolavine
Summary: <blockquote class="userstuff">
              <p>Sam wants to see Dean in Woman’s lingerie and Dean obliges. Inspired by <a href="http://www.livejournal.com/userinfo.bml?user=badbastions"><img class="i-ljuser-userhead"/></a><a class="i-ljuser-username" href="http://www.livejournal.com/userinfo.bml?user=badbastions"><b></b></a> ‘s cross dressed <a href="http://badbastion.livejournal.com/17585.html">Give us a Kiss Sweetheart</a></p>
            </blockquote>





	How’s this Mr. DeMille?

**Title:** How’s this Mr. DeMille?  
 **Author:** Dolavine  
 **Pairing** : Dean and Sam  
 **Rating:** Pg 13  
 **Word Count:** 1,173  
 **Disclaimer:** I don’t own anything, just like playing with the boys for non profit fun.  
 **Warnings:** Cross Dressing Dean Winchester  
 **Summary:** Sam wants to see Dean in Woman’s lingerie and Dean obliges. Inspired by [](http://www.livejournal.com/userinfo.bml?user=badbastions)[****](http://www.livejournal.com/userinfo.bml?user=badbastions)‘s cross dressed[Give us a Kiss Sweetheart](http://badbastion.livejournal.com/17585.html)  
 **PDF:** [AO3]()  
 **A/N:** Thanks for the Beta [](http://memoonster.livejournal.com/profile)[**memoonster**](http://memoonster.livejournal.com/) Thanks for the Inspiration [](http://badbastion.livejournal.com/profile)[**badbastion**](http://badbastion.livejournal.com/) you never fail to bring out my Muse.

 

Sam hands Dean a wrapped box with a tiny note attached. “What’s this for?” Dean plucks the note from behind the blue ribbon.

“Read the note,” Sam’s voice is soft and seductive.

Dean begrudgingly opens the envelope and reads the small handwritten note. “Put these on and pose for me,” he looks over at Sam with a confused expression.

“Just open the box Dean,” he waits for the box to be opened.

Dean opens the box and moves the white flaps of tissue paper to expose a black mesh thong, black stockings with a garter belt and a white flowing, very feminine, silk robe. “What the fuck,” he drops the box on the table before giving Sam an evil glare.

“You said, and I quote, _Whatever you want me to do, whatever kink you’ve been hiding up those plaid sleeves of yours, I’ll do._ end quote,” Sam cocks his eyebrow, folds his arms over his chest and crosses his ankle over his knee as he waits for the show.

“So your kink is for me to wear women’s lingerie and pose for you,” he says it like he can’t believe it.

“Uh-huh,” Sam doesn’t even nod, just stares right at Dean with a cocked eyebrow and smirk.

“Okay then,” he can’t argue with his own words so he, picks up the box and heads to the bathroom but Sam stops him. “Wait,” he says with a commanding tone. Dean turns around to see what he wants. “You’re going to do it right here in front of me, I want to watch you do it.”

“Shit Sammy,” Dean can’t deny it, he’s not even going to argue with him because the thought of Sam watching him put on lingerie, lingerie that he picked out for him, is turning him on immensely.

Dean’s completely clothed from his jacket to his boots and he knows that this is also going to be a striptease. He puts the box down on the bed and clears his throat. He’s not sure how sexily he can strip down, but he’s going to give it his best shot.

He slips his jacket off of his shoulders and lays it on the bed; he turns so that Sam can watch him undo each button of his flannel shirt. His fingers slowly plucking each pearly white button through the eyelet on their way down to the last one, he drops the shirt off of his broad shoulders before shimming it off of his arms then laying it on the bed. Sam shifts in his seat and lets out a slight sigh. Dean continues disrobing.

He pulls the dark cotton t-shirt over his belly, pulling it over his chest and then head before over his arms and giving it a place next to the first two pieces on the bed.

Now for his boots, those damned hard to pull off boots. He turns his behind to Sam and reaches down to unlace his boots, one at a time, and his ass is completely in Sam’s face the whole time. Sam runs his hand over his jaw then wipes his lower lip like he’s trying to control himself. Dean finally stands up and struggles to toes off his boots.

His Jeans are a different story; he pops the buttons from his waistband down his fly, each making a soft popping noise as they slip through the stretched and worn eyelets. Sam clears his throat as he intently watches Dean’s movements. Dean shimmies them off of his hips, down his legs, and onto the floor where he merely steps out of them and shoves them against the foot of the bed.

Sam’s almost drooling; Dean can tell he’s salivating at the idea of the loss of his boxers so he makes this the last thing as he slowly removes his socks, one at a time in a satisfyingly slow and torturous pace. Just knowing that Sam is literally chomping at the bit to see his, well, bits, is the very thing he’s getting out of this entire event.

Once he shoves his boxers down, freeing up his semi-hard manhood, he can see the relief on Sam’s face. Sam’s biting his lower lip as his eyes roam all over Dean’s well maintained muscular frame.

“On with the show,” Dean says coyly as he fingers the panties. He takes them out and slips them on, pulling them up slowly, letting the softness of them caress his legs and thighs before pulling them into place. He adjusts his dick upward to fall slightly against his hip. It’s still half hard and swollen enough to make quite a presence under the slightly see through fabric. Sam licks his lips and shifts uncomfortably in his seat. He’s moved his hand up to rest under his jaw line while he watches with interest.

Next is the garter belt. He’s not sure how this works, he’s seen enough of them on strippers but it seems more complicated to put on, than take off. He slips it up over his legs, adjusts it at his hips and makes sure the clips are over his thighs. ‘Seems right,” he says to himself.

The stockings are thin and sheer. His rough fingers catch on them and he hopes he doesn’t snag them. He slides one up his left leg, slowly stretching it over his bowed leg and over his thigh. He examines it for smoothness by running his hand over his calf. It seems smooth so he attaches the garter facets on to it. He repeats the process on the other leg and then examines them, pointing his toes and extending his legs. He glances over at Sam who is breathing a bit heavier, his tongue is wetting his red bitten lower lip and his cheeks are flushed.

He stands up and slips on the long flowing robe. The silk touches his skin and it tingles with anticipation, his cock hardens a bit more pressing against the panties causing a sheen to enhance the outline of his thick shaft. The flowing skirt billows around him as he pulls it on, shifts it over his broad shoulders and adjusts it.

He looks at himself in the heart shaped mirror over the vanity. His eyes go wide and he licks his lips. “Damn, this is sexy,” he whispers. He can see Sam watching him, roaming his body with those sultry hazel eyes. He smoothes his hands over the robe and then adjusts everything to perfection before reaching up and tussling his hair the best he can. He messes it up giving himself a softer more feminine look and then purses his lips, he doesn’t even care that he still has stubble; he just sucks in his cheeks and goes for all out sexy before turning around and facing Sam.

“Like what you see,” he asks with a soft sultry voice.

Sam just nods, he doesn’t say a word, just watches the show.

Dean walks over and sits down on an overstuffed chair in the corner. He fumbles a bit to look sexy, to pose like a pin up girl from the fifties, because he feels like a queen of the silver screen giving a screen test for some big named producer of the era.

He shifts his shoulders and the robe falls gently off one of them exposing his freckle peppered shoulder. He pulls his knees up and points his toes as he twists his waist and props himself forward with his hands flat on the seat of the chair. He blinks, tilts his head, looks down a little and cocks his eyebrow before giving Sam a slightly open mouthed smirk. “How’s this Mr. DeMille?”

The End


End file.
